Donghaecyclinones A-C: New Cytotoxic Rearranged Angucyclinones from a Volcanic Island-Derived Marine Streptomyces sp.
- Authors
- Bae, Munhyung; An, Joon Soo; Hong, Seong-Heon; Bae, Eun Seo; Chung, Beomkoo; Kwon, Yun; Hong, Suckchang; Oh, Ki-Bong; Shin, Jongheon; Lee, Sang Kook; Oh, Dong-Chan
- Issue Date
- Feb-2020
- Publisher
- MDPI
- Keywords
- molecular modeling; electronic circular dichroism; quantum mechanics-based computation; angucyclinone; Streptomyces; cytotoxicity
- Citation
- MARINE DRUGS, v.18, no.2
- Journal Title
- MARINE DRUGS
- Volume
- 18
- Number
- 2
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/83301
- DOI
- 10.3390/md18020121
- ISSN
- 1660-3397
- Abstract
- Chemical profiling of the Streptomyces sp. strain SUD119, which was isolated from a marine sediment sample collected from a volcanic island in Korea, led to the discovery of three new metabolites: donghaecyclinones A-C (1-3). The structures of 1-3 were found to be rearranged, multicyclic, angucyclinone-class compounds according to nuclear magnetic resonance (NMR) and mass spectrometry (MS) analyses. The configurations of their stereogenic centers were successfully assigned using a combination of quantum mechanics-based computational methods for calculating the NMR shielding tensor (DP4 and CP3) as well as electronic circular dichroism (ECD) along with a modified version of Mosher's method. Donghaecyclinones A-C (1-3) displayed cytotoxicity against diverse human cancer cell lines (IC50: 6.7-9.6 mu M for 3).
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